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Physiologically Active Compounds from Terpenoids

#3967


Synthesis of Physiologically Active Compounds via the Transformations of Terpenoids in Supercritical Solvents. From Preparative Syntheses to Technology

Tech Area / Field

  • CHE-IND/Industrial Chemistry and Chemical Process Engineering/Chemistry
  • ENV-WPC/Water Pollution and Control/Environment

Status
3 Approved without Funding

Registration date
17.04.2009

Leading Institute
Boreskov Institute of Catalysis, Russia, Novosibirsk reg., Akademgorodok

Collaborators

  • Universidade Nova de Lisboa / Faculdade de Ciencias e Technologia, Portugal, Lisbon\nPukyong National University, Korea, Busan\nUniversity of Birmingham / School of Chemical Engineering, UK, Birmingham\nProteoFluidics Inc., Canada, ON, Waterloo\nUniversity of Michigan / Colledge of Engeneering / Department of Chemical Engineering, USA, MI, Ann Arbor\nKumamoto University, Japan, Kumamoto\nUniversity of Saskatchewan / Department of Chemical Engineering, Canada, SK, Saskatoon\nForschungszentrum Karlsruhe in der Helmholts-Gemeinschaft, Germany, Karlsruhe

Project summary

The Project is aimed at developing new efficient methods and technologies for transformations of phytogenic monoterpenoids to synthesize new biologically active compounds with the use of supercritical solvents (reaction medium).

Monoterpenes and their oxygenated derivatives are selected as the subject of research. Intra- and intermolecular selective transformations of terpenoids, both with and without nanostructured catalysts, will be performed in the following supercritical solvents: C1-C3 alcohols, CO2, water, and in some saturated hydrocarbons and their mixtures (solvents), at temperatures and pressures slightly exceeding respective critical parameters of the reaction mixture. Since substances acquire unique properties in the critical region of their parameters, in some cases supercritical solvents provide a multiple acceleration of a chemical reaction and render its selectivity controllable.

Expected products of monoterpenoids conversion in supercritical CO2, alcohols, water, and their mixtures include optically active terpene ketols, which are greatly demanded as biologically active compounds and chiral ligand precursors. It is planned to focus the main attention on the intermolecular reactions of terpenoids with aldehydes, which yields chiral polycyclic compounds showing high physiological activity.

In contrast to reactions under ordinary conditions, transformations of phytogenic terpenoids in supercritical solvents will allow controllable process selectivity; high conversion degree and specified selectivity will be reached in several minutes; the use of ecologically unsafe chlorinated solvents will be avoided.

The project goal is to perform fundamental and applied studies for acquiring new knowledge on chemical transformations of selected natural organic compounds in supercritical fluids, particularly water, alcohols, CO2 and saturated hydrocarbons, and to develop on the basis of these knowledge new methods and technologies for the synthesis of rare and valuable organic substances and compounds (chiral polycyclic compounds in particular).

The proposed aims will be reached via experimental studies of transformations of selected organic compounds (monoterpenoids) in various supercritical solvents in the presence of heterogeneous nanocatalysts, or in catalyst absence. Experimental studies of the kinetics and mechanisms of terpenoid conversion, development of macrokinetic models of the reactions will facilitate evaluation of the effect of (co)solvent nature, temperature and pressure on the reaction rate over different routes, selectivity for target products both in inpidual supercritical solvents and in their mixtures.

Special attention will be focused on the effect of pressure, co-solvents and, in some cases, heterogeneous catalysts on the rate and selectivity of intra- and intermolecular transformations of terpenoids in supercritical solvents.

Laboratory experiments, mathematical modeling, thermodynamic and kinetic calculations concerning the basic problems of the Project will serve as the main instruments to implement this part of the Project, and as intermediate step towards the development of new preparative methods and technologies. Calculating and modeling will allow us to determine location and drift of the critical point of a multi-component fluid, to calculate chemically equilibrium composition of the mixture under the condition of its non-ideality, and to find the optimal conditions (solvent concentration, temperature, pressure) for running chemical reactions by the desired routes.

The Project participants possess rich experience in fundamental and applied researches and in successful collaboration with other institutions around the world. In recent years, the author team has published more than 50 research works on the project-related problems in the leading scientific journals. The team has created and put into operation the first Russian stationary SCWO plant intended for the oxidation and decomposition of a wide range of organic compounds.

The Project entirely complies with the ISTC aims and goals; it is aimed at solving national and international R&D problems and facilitates international integration of scientists and specialists in this field. The role of foreign collaborators in the proposed project is of key importance, because they, first, act as experts, and, second, possess experience and knowledge which will facilitate efficient solving of the stated project tasks.


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The International Science and Technology Center (ISTC) is an intergovernmental organization connecting scientists from Kazakhstan, Armenia, Tajikistan, Kyrgyzstan, and Georgia with their peers and research organizations in the EU, Japan, Republic of Korea, Norway and the United States.

 

ISTC facilitates international science projects and assists the global scientific and business community to source and engage with CIS and Georgian institutes that develop or possess an excellence of scientific know-how.

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